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Phosphine/N-heterocyclic carbene palladium complex for Suzuki-Miyaura cross-coupling reactions: The role of water on activity

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Abstract A new bidentate ferrocenyl phosphine/N-heterocyclic carbene (NHC) palladium complex rac-6, bearing a functionalized pendant arm for further grafting on a solid surface, has been synthesized in good yields and… Click to show full abstract

Abstract A new bidentate ferrocenyl phosphine/N-heterocyclic carbene (NHC) palladium complex rac-6, bearing a functionalized pendant arm for further grafting on a solid surface, has been synthesized in good yields and fully characterized. The molecular structure of proligand rac-4-BF4 and complex rac-6 were obtained by X-ray diffraction on single crystals. Kinetic studies demonstrated the good activity and stability of rac-6 in the Suzuki-Miyaura coupling of aryl bromides with arylboronic acids. The catalyst proved also to be active for the coupling of more challenging, bulky substrates such as 1-bromo-2-methylnaphthalene and naphthylboronic acid at relatively mild temperatures (40–70 °C) and low loadings (0.1–0.5 mol%). Experiments carried out with various amounts of water highlighted the role of water on both activity and mechanism.

Keywords: water; activity; heterocyclic carbene; suzuki miyaura; palladium complex; phosphine heterocyclic

Journal Title: Inorganica Chimica Acta
Year Published: 2019

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